2,5-二甲基-3,4-二苯基-己烷-3,4-二醇 | 6328-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,5-二甲基-3,4-二苯基-己烷-3,4-二醇
• 英文名称: Bis<1-(ethoxycarbonyl)ethyl> disulfide
• 英文别名: 2,5-dimethyl-3,4-dithia-adipic acid diethyl ester；2,5-Dimethyl-3,4-dithia-adipinsaeure-diaethylester；Dithiodilactylsaeure-diaethylester；Ethyl propionate, 2,2'-dithiobis-；ethyl 2-[(1-ethoxy-1-oxopropan-2-yl)disulfanyl]propanoate
• CAS: 6328-50-3
• 化学式: C₁₀H₁₈O₄S₂
• 分子量: 266.383
• InChiKey: NNHMMWUGCDHPAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  159 °C
• 沸点：
  14 °C
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-巯基丙酸乙酯 在 双氧水 、 sodium iodide 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 2,5-二甲基-3,4-二苯基-己烷-3,4-二醇
  参考文献：
  名称：

  烯烃与线性二硫化物的光二硫化：反应范围和动力学

  摘要：

  硫醇-烯和硫醇-炔光介导的共轭在研究和实践中受到了广泛关注。本文介绍了基于自由基介导的二硫化物和乙烯基醚的 1:1 反应的烯烃的光二硫化，这为硫醇-烯和硫醇-炔聚合物中所见的硫化物类型的形成提供了额外的途径。尽管形成了类似的键，但这种从二硫化物开始的方法预计比硫醇-烯和硫醇-炔反应具有优势，包括与硫醇相比延长二硫化物的保质期、降低收缩应力和提高所得材料的折射率。已确定乙烯基醚是唯一能够在环境条件和合理时间范围内进行光二硫化的烯烃。乙烯基醚和二硫化物之间的反应在各种溶剂中表现良好，为许多评估的二硫化物底物提供中等至优异的产率（双（1-甲基乙酸酯）二硫化物 (DSMA)/三乙二醇二乙烯基醚 (TEGDVE) 为 100%）。已确定光二硫化反应的机理涉及硫基自由基的自动传播循环，其添加到乙烯基醚的任一端以在最终产物中形成硫醚和硫缩醛键。最后，虽然反应速率比硫醇-烯反应慢，但在所探索的条件下，光二硫化反应进行得相对较快。

  DOI：

  10.1016/j.tet.2022.132683

文献信息

• Activation and synthetic applications of thiostannanes. Efficient conversion of thiol acetates into disulfides
  作者：Sato Tsuneo、Otera Junzo、Nozaki Hitosi

  DOI：10.1016/s0040-4039(00)94451-4

  日期：1990.1

  Thiostannanes are obtained by treating alkoxystannanes with thiol acetates. Coupled with this reaction, the thiostannane methodology enables one-pot synthesis of disulfides from thiol acetate.

  通过用硫醇乙酸酯处理烷氧基锡烷来获得硫氧烷。结合该反应，硫代锡烷方法学使得能够从乙酸硫醇单锅合成二硫化物。
• Additives for lubricating oils and fuel oils, lubricating oil compositions, and fuel oil compositions
  申请人：Shimizu Nobuaki

  公开号：US20060148663A1

  公开（公告）日：2006-07-06

  Additives for lubricating oils and for fuel oils which comprise as the main component a disulfide represented by the following general formula (I) or (IV): R 1 OOC-A 1 -S x -A 2 -COOR 2 (I) (R 1 and R 2 each independently represent a hydrocarbyl group which has 1 to 30 carbon atoms and may have oxygen atom, sulfur atom or nitrogen atom, A 1 and A 2 each independently represent a group represented by CR 3 R 4 , R 3 and R 4 each independently representing hydrogen atom or a hydrocarbyl group having 1 to 20 carbon atoms, and x represents 2.) R 1 OOC-A 3 -S x -A 4 -COOR 2 (IV) (R 1 and R 2 are as defined above, A 3 and A 4 each independently represent a group represented by CR 5 R 6 —CR 7 R 8 , R 5 to R 8 each independently representing hydrogen atom or a hydrocarbyl group having 1 to 20 carbon atoms, and x represents 2.) The additives exhibit excellent functions as the extreme pressure additive and the antiwear agent and the suppressed corrosive property to nonferrous metals and are advantageously used as the sulfur-based extreme pressure additives for lubricating oils and fuel oils.

  润滑油和燃料油的添加剂包括以下通式（I）或（IV）所表示的二硫化物作为主要成分： R1OOC-A1-Sx-A2-COOR2（I）（其中，R1和R2分别独立地表示具有1至30个碳原子且可能具有氧原子、硫原子或氮原子的烃基，A1和A2分别独立地表示CR3R4所表示的基团，R3和R4分别独立地表示氢原子或具有1至20个碳原子的烃基，x表示2。） R1OOC-A3-Sx-A4-COOR2（IV）（其中，R1和R2如上定义，A3和A4分别独立地表示CR5R6-CR7R8所表示的基团，R5至R8分别独立地表示氢原子或具有1至20个碳原子的烃基，x表示2。） 这些添加剂表现出极压添加剂和抗磨剂的优异功能，对非铁质金属具有抑制腐蚀性能，是用于润滑油和燃料油的硫基极压添加剂的有利选择。
• PROCESS FOR THE PREPARATION OF THIOL COMPOUNDS
  申请人：Nippon Shokubai Kagaku Kogyo Co., Ltd

  公开号：EP0825179A1

  公开（公告）日：1998-02-25

  In order to manufacture a thiol compound by causing reaction between an unsaturated compound and hydrogen sulfide, the unsaturated compound and the thiol compound being expressed by following formulas (1) and (2), respectively:         CH2 = CR1 - COOR2     (1)         HS - CH2 - CHR1 - COOR2     (2) where R1 represents a hydrogen atom or a methyl group, and R2 represents a hydrogen atom or a hydrocarbon group with 1 to 18 carbon atoms, (i) at least one nitrogen containing compound which is selected from the group consisting of amide compounds each having an amide group without a substituent, amide compounds each having an amide group whose nitrogen atom has a substituent hydrocarbon group with 1 to 6 carbon atoms, urea compounds each having an ureylene group without a substituent, and urea compounds in each of which at least one of two nitrogen atoms (N, N') has a substituent hydrocarbon group with 1 to 6 carbon atoms, and (ii) either a polysulfide compound or sulfur, or the both, are made to coexist in a system of reaction, the polysulfide compound being expressed by a following formula (3):         R4OOC - CHR3 - CH2 - SX - CH2 - CHR3 - COOR4     (3) where R3 represents a hydrogen atom or a methyl group, R4 represents a hydrogen atom or a hydrocarbon group with 1 to 18 carbon atoms, and x represents an integral number of 2 to 5. By doing so, a smooth reaction between the unsaturated compound and hydrogen sulfide can be caused, and the thiol compound can be produced at a high selectivity and a high yield.

  为了通过使不饱和化合物与硫化氢发生反应来制造硫醇化合物，不饱和化合物和硫醇化合物分别用以下公式（1）和（2）表示： ch2 = cr1 - coor2 (1) HS - CH2 - CHR1 - COOR2 (2) 其中 R1 代表氢原子或甲基，R2 代表氢原子或 1 至 18 个碳原子的烃基，(i) 至少一种含氮化合物，该化合物选自由下列化合物组成的酰胺化合物，每种酰胺化合物都具有一个不带取代基的酰胺基，每种酰胺化合物都具有一个氮原子带有 1 至 6 个碳原子的烃基取代基的酰胺基、(ii) 多硫化物化合物或硫，或二者共存于反应体系中，多硫化物化合物用下式(3)表示： R4OOC - CHR3 - CH2 - SX - CH2 - CHR3 - COOR4 (3) 其中，R3 代表氢原子或甲基，R4 代表氢原子或碳原子数为 1 至 18 的烃基，x 代表 2 至 5 的整数。 这样，不饱和化合物与硫化氢就能顺利反应，并能以高选择性和高产率生产硫醇化合物。
• ADDITIVES FOR LUBRICATING OILS AND FUEL OILS, LUBRICATING OIL COMPOSITIONS, AND FUEL OIL COMPOSITIONS
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：EP1602709A1

  公开（公告）日：2005-12-07

  Additives for lubricating oils and for fuel oils which comprise as the main component a disulfide represented by the following general formula (I) or (IV):         R1OOC-A1-Sx-A2-COOR2     (I) (R1 and R2 each independently represent a hydrocarbyl group which has 1 to 30 carbon atoms and may have oxygen atom, sulfur atom or nitrogen atom, A1 and A2 each independently represent a group represented by CR3R4, R3 and R4 each independently representing hydrogen atom or a hydrocarbyl group having 1 to 20 carbon atoms, and x represents 2.)         R1OOC-A3-Sx-A4-COOR2     (IV) (R1 and R2 are as defined above, A3 and A4 each independently represent a group represented by CR5R6-CR7R8, R5 to R8 each independently representing hydrogen atom or a hydrocarbyl group having 1 to 20 carbon atoms, and x represents 2.) The additives exhibit excellent functions as the extreme pressure additive and the antiwear agent and the suppressed corrosive property to nonferrous metals and are advantageously used as the sulfur-based extreme pressure additives for lubricating oils and fuel oils.

  用于润滑油和燃油的添加剂，其主要成分是由以下通式 (I) 或 (IV) 所代表的二硫化物： R1OOC-A1-Sx-A2-COOR2 (I) (R1 和 R2 分别独立地代表具有 1 至 30 个碳原子并可能具有氧原子、硫原子或氮原子的烃基，A1 和 A2 分别独立地代表 CR3R4 所代表的基团，R3 和 R4 分别独立地代表氢原子或具有 1 至 20 个碳原子的烃基，x 代表 2)。 R1OOC-A3-Sx-A4-COOR2 (IV) (R1 和 R2 如上定义，A3 和 A4 各自独立地代表一个由 CR5R6-CR7R8 所代表的基团，R5 至 R8 各自独立地代表氢原子或具有 1 至 20 个碳原子的烃基，x 代表 2）。这些添加剂具有优异的极压添加剂和抗磨剂功能以及对有色金属的抑制腐蚀性能，可作为润滑油和燃料油的硫基极压添加剂使用。
• Synthesis of Disulfides by Copper-Catalyzed Disproportionation of Thiols
  作者：Jaesung Choi、Nung Min Yoon

  DOI：10.1021/jo00116a001

  日期：1995.6